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Sigma-Aldrich

Dichloromethylene-dimethyliminium chloride

technical grade

Synonym(s):

(Dichloromethylene)dimethylammonium chloride, Phosgeniminium chloride, Vilsmeier reagent

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About This Item

Linear Formula:
[Cl2C=N(CH3)2]+Cl-
CAS Number:
33842-02-3
Molecular Weight:
162.45
Beilstein:
4157987
EC Number:
251-695-4
MDL number:
MFCD00011870
UNSPSC Code:
12352100
PubChem Substance ID:
24850009
NACRES:
NA.22

grade

technical grade

mp

183-187 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

[Cl-].C\[N+](C)=C(\Cl)Cl

InChI

1S/C3H6Cl2N.ClH/c1-6(2)3(4)5;/h1-2H3;1H/q+1;/p-1

InChI key

NRNFKRFWZQQDMD-UHFFFAOYSA-M

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General description

Dichloromethylene-dimethyliminium chloride (Vilsmeier reagent) reacts with o-acetaminophenols under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles.

Application

Dichloromethylene-dimethyliminium chloride was used as reagent in the synthesis of selenourea and (R)-2-(2-chloroethyl)pyrrolidine-1-carboxylic acid ethyl ester. It was used for introducing amide chloride group into activated substrates.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A facile synthesis of N/C-terminal selenourea tethered glycosylated amino acids.
Sureshbabu VV, et al.
Indian J. Chem. B, 52(7), 895-900 (2013)
Asymmetric transformation of L-homoserine lactone to an optically active 2-substituted pyrrolidine for clemastine.
Kim SJ, et al.
Tetrahedron Asymmetry, 22(20), 1901-1905 (2011)
J. Prakt. Chem./Chem.-Ztg., 336, 561-561 (1994)
Ke-Lai Li et al.
The Journal of organic chemistry, 74(9), 3286-3292 (2009-04-01)
o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2'-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,1-b]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by
Ruhamah Yunis et al.
Physical chemistry chemical physics : PCCP, 21(23), 12288-12300 (2019-05-30)
The synthesis and characterisation of new solid-state electrolytes is a key step in advancing the development of safer and more reliable electrochemical energy storage technologies. Organic ionic plastic crystals (OIPCs) are an increasingly promising class of material for application in

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